BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD)
BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD)
8th Edition
ISBN: 9781337687539
Author: Brown/Iverson/Anslyn/ Foote
Publisher: CENGAGE C
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Chapter 28, Problem 28.7P
Interpretation Introduction

Interpretation:

The structural formulas for the enethiol forms of 6-mercaptopurine and 6-thioguanine has to be drawn.

Concept Introduction:

The functional group ketone (keto group) will be in equilibrium with the enol (alcohol group) form which is said to be the keto-enol tautomerization.  The keto form is more stable when compared to the enol form. The keto-enol conversion reaction is

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 28, Problem 28.7P , additional homework tip  1

Expert Solution & Answer
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Explanation of Solution

The enethiol is also the enol form which contains Sulphur molecule instead of Oxygen.  The enethiol form is the alcoholic form of the Sulphur.  The double bonded Sulphur is converted to thiol form of the Sulphur.

The enethiol form of 6-mercaptopurine is

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 28, Problem 28.7P , additional homework tip  2

The enethiol form of 6-thioguanine is

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 28, Problem 28.7P , additional homework tip  3

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A pioneer in designing and synthesizing antimetabolites that could destroy cancer cells was George Hitchings at the Burroughs Wellcome Company. In 1942, he initiated a pro- gram to discover DNA antimetabolites, and in 1948, he and Gertrude Elion synthesized 6-mercaptopurine, a successful drug for treating acute leukemia. Another DNA antime- tabolite synthesized by Hutchings and Elion was 6-thioguanine. Hitchings and Elion along with Sir James W. Black won the 1988 Nobel Prize in Physiology or Medicine for their discoveries of "important principles of drug treatment." In each drug, the oxygen at carbon 6 of the parent molecule is replaced by divalent sulfur. Draw structural formulas for the enethiol (the sulfur equivalent of an enol) forms of 6-mercaptopurine and 6-thioguanine. HN HN H,N H 6-Mercaptopurine 6-Thioguanine
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